Monoazodyestuffs



UNITED TATES o frlcE" WINFRID HEN-TRICK, or wIEsnoR-F-oN-r E-RHmE, niiiidnnegnocnn og" LEVER- KUSEN-ON-THE-RHINE, AND ERNST TIETZE, E-"conocirn-on-rma-amnn, GERMANY, AssIGNoRs 'ro GENERAL ANIVLINE worms, 1110., SOFAINEWLYORK;,\NI Y., A conro- EATION OF DELAWARE MONOAZODYES Urns No Drawing. Application filed November 23, 1928,Serial N0. a21,5i12-,.=ana-in Germany Nbveniber 293927.; 7

' Our present invention relates to new monoazo dyestuffs capable of being chromed, more particularly it relatesito dyestu-fl's of the following probable general formula:

m OOH, v

10 wherein the nucleus marked I may be substituted by halogen. V

The new dyestuffs are obtainable by diazotiz'ing an ortho-aminophenol sulfonic acid of the formula v HOaS or a halogen substitution product thereof and combining the diazo compound in an acid medium with Z-naphthylamine 3-carboxylic acid. They are in form of their alkali metal salts dark reddish brown powders, easily soluble in water with ared coloration. When treated with stannous chloride and hydrochloric acid they are split up to the corresponding o-amino-phenol-sulfonic acid and 1.2 naphthylenediamine 3 oarboxylic acid.

They dye wool red shades, which change to a .green shade of apurity hitherto unobtainable in this class of dyestulfs by after-chroming the original dyeings according to usual methods. The-dyeings are Very fast to light, sulfur, fulling, steaming and carbonization. The following example illustrates our in vention, without limiting it thereto Example-487 parts by weight of thylamine-3-carboxylic acid are dissolved in water with the aid of alkali and the diazo solution, obtained by diazotizing 223 parts by weight of 4-chloro-2-amino-1-phenol-6-" sultonic acid in diluted hydrochloric acid, is added thereto while; vigorously 1 stirring. Pyridine is then added ,until the. solution is only faintly acidto Congo red; When' the' coupling is complete, the dyestufl is conyertr, ed by means of ammonia into theammonium salt, which is salted out, pressed-and dried.

ably corresponds in mula:

forms reddish brownipowder eas' y in water in form of its'sodiuin 's'alt'with a red" coloration, it dyes wool a red shade from an acid bath and, when chromed on-the fiber,

yields a very clear yellowish green shade, v

which withstands very satisfactorily'normal and strong fulling and possesses satisfactory fastness to sulfur, steaming and carbonization and excellent fastness to light.

' When treated with stannous chloride and i hydrochloricacid the dyestufi' is split up to 2 amino- 4: -chloro 1 hydroxybenzene 6 -'sulfonic acid. and 1.2-naphthylene diaminesii- I carboXylic acid.

' Dyestufls of similar properties can be obobtain'ableg which Y '5 :its free form to the fortained by replacing the l-chloro-Q-amino- I phenol-G-sulfonic'acid by, for example, the 5 sulfonic acid or by 2-amino-phenol--sulfonic acid.

q We claim:

formula Hogs colorations, dyeing woolfrom an acid ibath chroming, yielding when treated with stannou's chloride and hydrochloric acid an 1. As new "compounds, o-hydrox'y-mono azo dyestufls capable of being chromed, hav- 7 1 ing in their free form the probable general V o-amino -phenol-sulfonic acid and l.2-naphthylenediamine-3-carboxylic acid.

2 As a new compound, the o-hydroxymono-azo dyestuff capable of bein chromed, havling in its free form the pro able formu a:- 7 Y v 1 said dyestuff being in form of its sodium salt a reddish brown powder, easily soluble in water with a red coloration, dyeing wool from an acid bath a red shade, which changes to a clear green of good fastness properties by after-chroming.

3. Material dye with a claim 1.

4, Material dyed with the dyestuff claimed in claim 2. i

In testimony our hands.

dyestufl? claimed whereof we have hereunto set :WINFRID HENTRICH. 1 3. RUDOLF KNOCHE. [L. s.]

ERNST TIETZE. 

